Oakland Holiday Rentals

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Our top choices for Oakland holiday rentals

10.0 out of 10, Exceptional, (1)
"The place was amazing and so comfortable! Loved the airiness feeling. The neighbor hood was family friendly and quiet. The host was amazing and super helpful. Place was super clean and had everything we needed...our dogs loved the fenced backyard...being able to roam freely. Check in and check out was super easy...lots of shopping and eateries up the street. Will definitely book here again! A"
United States
Angie G.
The price is AU$400
includes taxes & fees
6 Jan - 7 Jan 2026
Modern Retreat in the Heart of Royal Oak
10.0 out of 10, Exceptional, (3)
The price is AU$384
includes taxes & fees
31 Dec - 1 Jan 2026
This property offers a clean and comfortable modern vibe with updated furniture and decorations
9.2 out of 10, Wonderful, (7)
"Nice stay "
United States
Amanda M.
The price is AU$442
includes taxes & fees
19 Dec - 20 Dec
The Drift House- Spacious Boho Family Retreat- 4 bds, 2 baths, 6 TVs, Movie Room
10.0 out of 10, Exceptional, (8)
"House was as advertised. Close to several local restaurants and bars. "
United States
James S.
The price is AU$288
includes taxes & fees
22 Dec - 23 Dec
Welcome to, Days Inn Paradise located in Clinton Townshipship Michigan.
9.2 out of 10, Wonderful, (9)
"Nice relaxing country setting. "
United States
Jon B.
The price is AU$446
includes taxes & fees
21 Dec - 22 Dec
Charming old farmhouse, spacious 2-bedroom on 2+ acres

Holiday Home in West Bloomfield Township

Luxury Guest place: very close to lake and downtown
7.6 out of 10, Good, (22)
"Amazing "
United States
Demarco F.
The price is AU$343
includes taxes & fees
19 Dec - 20 Dec
Luxury Guest place: very close to lake and downtown
9.4 out of 10, Exceptional, (13)
"The stay was great! "
Canada
Dustin L.
The price is AU$229
includes taxes & fees
21 Dec - 22 Dec
Air-Conditioned Studio | Pool
10.0 out of 10, Exceptional, (1)
"It was fun"
United States
Michael D.
The price is AU$327
includes taxes & fees
21 Dec - 22 Dec
Charming and Spacious 3-bedroom House with WiFi, AC in nice Ferndale, MI
9.8 out of 10, Exceptional, (6)
"This was a great spot on the lake with a cozy fireplace. Great if your hunting in local area and also want to get some fishing in."
United States
Paula
The price is AU$383
includes taxes & fees
19 Dec - 20 Dec
Cozy 2-bedroom bungalow on Lake St Clair with plenty of room to dock your boat!
9.2 out of 10, Wonderful, (57)
"My sisters and I visit my mom in her twice a year"
United States
Pamela N.
The price is AU$455
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious Farmhouse with Breakfast- Ella’s Place
10.0 out of 10, Exceptional, (7)
"Loved this house! Perfect amount of space for our family and very clean and comfortable. Loved the organizers in the closet and bathroom too!"
United States
Kelly L.
The price is AU$440
includes taxes & fees
13 Jan - 14 Jan 2026
Colorful Retreat, w/ Firepit and 2 TV's. By Royal Oak!
9.4 out of 10, Exceptional, (52)
"Overall a great value for the location. Easy in and out checkin/checkout. Comfy beds and everything you need in the kitchen for an at home stay. "
United States
Pat D.
The price is AU$311
includes taxes & fees
8 Jan - 9 Jan 2026
2BR Family-Sized Lower Suite with Private Entrance & Big Backyard. Pet-Friendly!
10.0 out of 10, Exceptional, (2)
"He brought out snacks for us, was a really friendly welcoming. Nice and clean house"
United States
Raina H.
The price is AU$614
includes taxes & fees
22 Dec - 23 Dec
Family Home with plenty of parking and long stay friendly. Fenced in Yard.
10.0 out of 10, Exceptional, (8)
"It was amazing very clean nice neighborhood, will be booking again!"
United States
Ahshyla F.
The price is AU$380
includes taxes & fees
19 Dec - 20 Dec
Charming 3-bedroom house with WiFi, fitness room in Pontiac

Holiday Home in Sterling Heights

Elegant 3BD Retreat in Sterling Heights
8.0 out of 10, Very good, (3)
"The house overall was great! Location, clean, and neighborhood. Only issues were there was only 2 rolls of toilet paper, 1/2 roll of paper towel, and 2 garbage bags. If we were supposed to bring our own i wish it was noted. The shower was difficult to figure out. The way the house is built with wood floors, you can hear everything from all the rooms. We would totally rent again, but we'd just be more prepared. "
United States
Teresa R.
The price is AU$426
includes taxes & fees
7 Jan - 8 Jan 2026
Elegant 3BD Retreat in Sterling Heights
The price is AU$371
includes taxes & fees
2 Jan - 3 Jan 2026
New! Spacious 1BR Flat in the Heart of Royal Oak
2.0 star property
9.4 out of 10, Exceptional, (6)
"“We had such a wonderful stay! The property was exactly as described—clean, comfortable, and stocked with everything we needed. The location was convenient, and the host was very responsive and made the process so easy. We’d definitely stay here again!”"
United States
Lisa E.
The price is AU$505
includes taxes & fees
19 Dec - 20 Dec
Luxury Downtown Retreat - Prime Spot - Sleeps 6

Holiday Home in rochester hills

private and spacious
10.0 out of 10, Exceptional, (82)
"Beautiful home, very kind hostess. Enjoyed our stay very much !"
United States
Kathy J.
The price is AU$226
includes taxes & fees
21 Dec - 22 Dec
private and spacious
10.0 out of 10, Exceptional, (18)
"We had a great stay. The house was perfect for our visit, great accommodations and we’ll be booking again for next year. Thank for a wonderful experience. "
United States
Coureen R.
The price is AU$499
includes taxes & fees
21 Dec - 22 Dec
☀️ Kissed by Sunshine ☀️ 3BDR Ranch by Royal Oak & Ferndale - Family Friendly 2TVs

Apartment in Birmingham

Premier Birmingham Retreat
10.0 out of 10, Exceptional, (4)
"Good location; clean"
United States
Teresa W.
The price is AU$416
includes taxes & fees
4 Jan - 5 Jan 2026
Premier Birmingham Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oakland Hotel Reviews

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as AU$121 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakland has to offer?

Cozy 2-bedroom bungalow on Lake St Clair with plenty of room to dock your boat!: This holiday home rental outside of Oakland offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What’s there to see and do in Oakland?

Explore the area and family-friendly sights such as Canterbury Village, or get out into nature at a spot like Addison Oaks County Park. Other places in town to visit include Bald Mountain State Recreation Area and Twin Lakes Golf Course.

What’s a holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family trips.